“As you get older, that [playboy] image isn’t as cute anymore, not like when you’re 18 and going out with a bunch of girls,” Clooney said years ago. “When you’re 40 and you do it, it’s kind of sad.”

It could be that he hadn’t found the right girl until now. Let’s take a look back at some of the actor’s previous ladies and the reasons they didn’t work out.

Dedee Pfeiffer

Why it didn’t work out: Because Clooney had a perm back then? But no. Seems the two parted ways amicably. Michelle would say years later that her sister still spoke kindly of her ex. “He was certainly not as narcissistic and self-centered as some I’ve worked with,” Michelle told Vanity Fair. “He doesn’t take himself that seriously.”

Kelly Preston

Photo: WireImage

Clooney moved in with the actress in 1988. The two would soon split, and Preston would marry John Travolta in 1991.

Why it didn’t work out: The couple owned a pet pig together, which might have come too close to family life for avowed bachelor George.

Talia Balsam

Photo: WireImage

The “Batman & Robin” star married actress Talia Balsam in 1989. The two had dated in 1984, but Balsam dumped him. The couple got back together a few years later and tied the knot in Vegas. They divorced in 1993.

Why it didn’t work out: Clooney blames himself. “I probably — definitely — wasn’t someone who should have been married at that point,” he told Vanity Fair. “I just don’t feel like I gave Talia a fair shot.”

The actor’s health was also poor during the marriage. He suffered from a bleeding ulcer and was in a bad place.

Kimberly Russell

Photo: WireImage

Clooney hooked up with the actress, who starred in the TV series “Head of the Class” and had a bit part on “ER,” in 1994.

Why it didn’t work out: The usual reason. George wasn’t ready to settle down.

“Don”t mention marriage or commitment or babies to George,” Russell later told the UK’s Sunday Mirror. “We’d been together for over three years, and I wanted a family. I wanted us to be man and wife. But there was no hope of pinning him down. He had one busted marriage already, and he told me flat out it was never going to happen again.”

Celine Balitran

Photo: WireImage

He met the French waitress in Paris while shooting “The Peacemaker” in 1996. The couple parted ways in 1999.

Why it didn’t work out: Clooney got restless again. “She lasted as long as I think she was going to last,” he later told Esquire. “It was like, ‘I don’t really think I want to play anymore.’ ”

The relationship also suffered due to Clooney’s busy schedule and high profile. When the two were able to see each other, Balitran had to contend with the paparazzi. She was instructed to drive by Clooney’s house first, to make sure no one was tailing her, before pulling in.

“I’ve actually said to her, ‘Hang in there,’ ” Clooney said. “Dating me is a hassle.”

Krista Allen

Photo: WireImage (left); Zuma Press (right)

He met the “Baywatch” babe in 2002 on the set of “Confessions of a Dangerous Mind.” Two years later, it was splitsville.

Why it didn’t work out: Allen reportedly complained that it was hard to spend time with her beau. When he did return to Los Angeles after weeks away, Clooney would opt to have dinner with friends, then head to Allen’s place for a nightcap, the National Enquirer reported. He also broke a promise to spend Christmas and New Year’s Eve in Mexico with her.

“What am I, just his friend with benefits?” Allen reportedly whined to friends.

Lucy Liu

Photo: FilmMagic

The two reportedly shared a kiss outside a New York restaurant in 2006.

Why it didn’t work out: It’s not even clear the two were ever dating. Liu has denied it.

Lisa Snowdon

Photo: WireImage

Clooney met the British model/actress on a commercial set in 2000, launching an on-again, off-again affair that lasted five years.

Why it didn’t work out: If reports are to be believed, it was Clooney who wanted to get more serious and was rebuffed by Snowdon, in part because she didn’t want to move from the UK to Los Angeles.

Sarah Larson

Photo: Reuters

Clooney picked up the Vegas cocktail waitress after a wild night out in 2007. They called it quits in 2008.

Why it didn’t work out: Sounds like Clooney’s wanderlust got the better of him again. Larson has said the breakup was unexpected.

“It was quick,” Larson told “Access Hollywood.” “You know, breakups are difficult, but people, you know, we move on, go on to other things.”

Larson has said she and Clooney no longer speak.

Elisabetta Canalis

Photo: Startraks Photo

He dated the Italian model from 2009 until 2011.

Why it didn’t work out: “At the end of the day I have always seen the end of my relationships as a personal failure,” Canalis told Italian magazine Chi. “There is nothing ever pretty in saying goodbye.”

Canalis was reportedly ready to settle down, but bachelor Clooney said no. She later blamed her choice in men.

“I have always seen cold and controlled men as the right ones for me,” she told Chi. “You have to accept that Prince Charming who is coming to save you is not going to happen. It works against you.”

Stacy Keibler

Photo: WireImage

He got together with Keibler, a former professional wrestler, in 2011. The couple broke up in July 2013.